Abstract
A multipurpose chemical modification of cellulose to yield soluble cellulose derivatives was investigated on the basis of (i) O-acylation of the parent cellulose using N-Boc-protected Gly, αAla, and βAla, and subsequent Boc-removal, (ii) N-acylation of amino acid-modified cellulose in homogenous solution reaction system using Boc-oligopeptides with multiple types of the side-chain functionalities, and (iii) N-acylation of βAla-Cellulose using 10 kinds of simple Boc-oligopeptides. As for the (i), Thermochemical computation to estimate ΔG transition was well coincided with the observed yields in Oacylations. In the case of (ii), beside the similar ΔG-schemes, a strain energy profile, which is coupled with the preferred conformer transition of the amino acid-modified cellulose, was involved to rule out the N-acylation. The symmetric anhydrate in the N-acylating agents in the (iii) are tend to be in torsions due to the β-strand-like steric stabilizations in the peptides, resulting in the highest N-acylation yields as much as 98 %.
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References
T. Heinze and T. Liebert, Prog. Polym. Sci., 26, 1689 (2001).
T. F. Liebert and T. Heinze, Biomacromolecules, 6, 333 (2005).
K. Ohkawa, M. Nishibayashi, K. Devarayan, M. Hachisu, and J. Araki, Int. J. Biol. Macromol., 53, 150 (2012).
K. Devarayan, M. Hachisu, J. Araki, and K. Ohkawa, Cellulose, 20, 1 (2012).
K. Devarayan, T. Hayashi, M. Hachisu, J. Araki, and K. Ohkawa, Carbohyd. Polym., 94, 468 (2013).
M. Hanwell, D. Curtis, D. Lonie, T. Vandermeersch, E. Zurek, and G. Hutchison, J. Cheminformat., 4, 17 (2012).
H. Goto and E. Osawa, J. Chem. Soc. Perkin Trans., 2, 187 (1993).
H. Goto and E. Osawa, J. Am. Chem. Soc., 111, 8950 (1989).
T. A. Halgren, J. Comput. Chem., 20, 720 (1999).
T. A. Halgren, J. Comput. Chem., 17, 490 (1996).
U. Burkert and N. L. Allinger, “Molecelar Mechanics”, American Chemical Society, Washington, DC, 1982.
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. J. A. Montgomery, J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudi, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox, “Gaussian 09, Revision A.1”, Gaussian, Inc., Wallingford CT, 2009.
J. P. Stewart, J. Mol. Model., 13, 1173 (2007).
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Ohkawa, K., Hachisu, M., Devarayan, K. et al. Design and synthesis of peptide-cellulose conjugate molecules —Aspects from energy/steric profiles—. Fibers Polym 14, 1970–1974 (2013). https://doi.org/10.1007/s12221-013-1970-x
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DOI: https://doi.org/10.1007/s12221-013-1970-x